Diisopropylethylamine → HCID 178432144, compound

HRID 1056351Notes

Reaction equation

HRID 1056351 reaction equation
[C:1]([NH:5][C:6]1[C:7]([CH3:24])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:20][N:19]=[C:18]([C:21](O)=[O:22])[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl.[Cl:35][CH2:36][CH2:37][NH2:38].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C=O)C.C(Cl)Cl>[C:1]([NH:5][C:6]1[C:7]([CH3:24])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:20][N:19]=[C:18]([C:21]([NH:38][CH2:37][CH2:36][Cl:35])=[O:22])[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 97937372-Chloroethylamine hydrochlorideHCID 178432145HCID 178432145, compound

Product 1

HCID 178432144HCID 178432144, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a 50-mL round-bottomed flask was added 5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrazole-3-carboxylic acid (467b) (69 mg, 0.21 mmol), DCM (4 mL), DMF (1 mL), DIPEA (0.15 mL, 0.85 mmol), 2-chloroethanamine hydrochloride (49 mg, 0.42 mmol) (Sigma-Aldrich), and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (110 mg, 0.21 mmol) (Sigma-Aldrich). The reaction mixture was stirred at RT for 16 h and the solvent was completely remover under vacuum. 5-(3-(tert-Butylamino)-2-methylquinoxalin-5-yl)-N-(2-chloroethyl)-1H-pyrazole-3-carboxamide (471a) was taken to next step without purification. m/z (ESI, +ve) 387.0 (M+H)+.

Workup

  1. custom5-(3-(tert-Butylamino)-2-methylquinoxalin-5-yl)-N-(2-chloroethyl)-1H-pyrazole-3-carboxamide (471a) was taken to next step without purification

Sources & evidence

ORD record
ord-0d17f41229e24275af78a30a842f44fb
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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